Regioselective Friedel−Crafts Alkylation of Anilines and Amino‐Substituted Heteroarenes with Hexafluoroacetone Sesquihydrate

Abstract

A variety of arenes, including anilines, pyrroles, indoles, aminooxazoles, aminothiazoles, aminoquinolines, and aminopyridines, underwent regioselective Friedel−Crafts alkylation in neat hexafluoroacetone sesquihydrate in a broad range of temperatures, reaction times, and yields (2%−94%) depending strongly on the electron density of the substrate. Prior N,N-dibenzylation of aniline and 2-aminopyridine

Design, synthesis and insecticidal activity of novel analogues of flubendiamide containing alkoxyhexafluoroisopropyl groups

“…These intermediates and title compounds were readily synthesized according to the reported methods. 26,[31][32][33] In some case, slight modications of these reaction conditions were necessary in order to obtain satisfying yields (see ESI † for details).…”

Regioselective C3-Fluoroalcoholation of Indoles with Heptafluoroisopropyl Iodide via Palladium-Catalyzed C(sp2)–C(sp3) Cross-Coupling in the Presence of O2

“…They also could be utilized for further elaboration of various fluorinated functional products . Current synthetic strategies for the introduction of the hexafluoropropan-2-ol into a target molecule basically comprise two alternative strategies: Friedel–Crafts alkylation of hexafluoroacetone or direct C–C coupling with hexafluoropropanol (Figure b) . However, using halogenated fluoroalkyl compounds as the source of fluoroalcohol to perform direct C­(sp 2 )–C­(sp 3 ) coupling reactions has been undeveloped.…”